I saw about 10 CROs leave or get fired this year across the startups I work with or have invested in at SaaStr Fund.
That’s a lot. That’s actually a ton. It may be a record. I suspect it is.
And look, some CRO transitions are natural. The company outgrows them. They want to go back to an earlier stage. The fit just wasn’t right from Day One. It wasn’t the right fit from Day 1. Those happen.
But most of what I saw this year? Those weren’t natural transitions. Those were flame-outs. Talented executives who came in with strong resumes, good references, and real experience — who just couldn’t make it work.
So I took a step back and asked myself: what actually went wrong? What were the patterns?
#1. They Never Sold The Product Themselves — They Just Managed the Team
This is the single biggest one I saw this year.
The CRO comes in with a great playbook. They’ve scaled teams before. They know how to hire, how to build comp plans, how to run QBRs. They set up the dashboards. They implement the methodology.
And then… nothing really changes. Or worse, things get worse.
Why? Because they never actually sold the product themselves.
They never got on calls with prospects. Never ran a full sales cycle from discovery to close. Never felt the objections in their gut. Never understood why deals were really stalling.
Here’s the thing: you cannot coach what you cannot do.
The best CROs I’ve worked with? First 30 days, they’re carrying a bag. They’re jumping on every call they can. They’re doing demos. They’re sending follow-up emails. Not because they have to hit quota — but because they need to understand.
They need to feel the product-market fit (or lack thereof) in their bones. They need to know which objections are real and which are just noise. They need to understand the actual buyer psychology for this product, not the last product they sold.
When a CRO only manages and never sells, they end up giving advice that sounds right but doesn’t work. They implement processes from their last company that don’t fit. They hire reps who would’ve crushed it at their old company but can’t close here.
If your CRO hasn’t personally closed at least 5-10 deals in their first 90 days, you’ve got a problem brewing.
#2. They Never Learned The Product Cold
This one is related but distinct.
I’m not talking about knowing the pitch deck. I’m not talking about being able to give the standard demo. I’m talking about knowing the product cold.
Can they answer the hard technical questions without calling in an SE? Do they understand the implementation process deeply enough to set proper expectations? Can they speak credibly to a technical buyer about architecture, security, integrations?
The CROs who flamed out? They stayed surface-level. They knew enough to have a conversation but not enough to have credibility. And sophisticated buyers — especially in enterprise — can smell that from a mile away.
I watched one CRO lose a seven-figure deal because they couldn’t answer basic questions about data residency in a meeting with the CISO. The SE wasn’t in the room. The CRO tried to tap-dance. The deal died.
The best CROs become product experts. Not because they need to replace the SE — but because deep product knowledge changes everything about how you sell. It changes what you emphasize. It changes how you handle objections. It changes which deals you pursue and which you walk away from.
If you can’t go deep on the product, you’ll never go deep on the deals.
#3. They Never Learned The Partner Channel
Partner channels are different than direct sales. They have their own dynamics, their own economics, their own politics. They take time to understand. They take relationships to unlock.
And a lot of CROs just… don’t bother.
They come in focused on the direct sales motion. They see partner as someone else’s problem — maybe there’s a partnerships team, maybe it’s a BD function, whatever. It’s not their core focus.
But here’s the reality: at most B2B SaaS companies past $10M ARR, partners influence a huge chunk of the pipeline. Often 30%-40% (e.g., HubSpot and Shopify). Sometimes more., Sometimes it’s channel partners. Sometimes it’s technology partners. Sometimes it’s consultants and agencies. Sometimes it’s all three.
When a CRO doesn’t understand the partner ecosystem, they make bad decisions constantly. They set direct quotas that conflict with partner incentives. They hire reps who can’t work with partners. They set up comp plans that actively discourage partner-sourced deals.
The CROs who flamed out on this one? They’d sit in pipeline reviews and literally not understand where 30-40% of the opportunities were coming from or how to accelerate them.
You don’t have to be a partnerships expert. But you have to understand your partner channel well enough to build a sales strategy that incorporates it — not fights against it.
#4. They Never Visited Enough of Their Team in Person
Okay, I know this sounds old-school. I know we’re in the remote-first era. I know travel is expensive and time-consuming.
I don’t care. This one is real.
The CROs who flamed out this year? Many of them were managing distributed teams largely from behind a Zoom screen. And it showed.
Here’s what happens when you don’t visit your team in person:
- You don’t really know who your top performers are (you only know who looks like they’re performing on calls)
- You don’t understand the local market dynamics in different regions
- You don’t build the kind of loyalty that keeps good reps from leaving
- You miss the early warning signs of cultural problems
- You don’t understand why certain offices or teams are struggling
I watched one CRO who had a team across four cities and visited each city maybe once in 18 months. They were genuinely surprised when their best AE in Chicago quit. “I had no idea they were unhappy.” Of course you didn’t — you never bothered to actually be there.
Sales is a human business. Always has been, always will be. And you cannot lead humans you never actually spend time with.
The best CROs I know are on the road constantly. Yes, it’s exhausting. Yes, it’s expensive. But they know that the deals get done in the field, the culture gets built in person, and the trust gets earned face-to-face.
Budget for the travel. Make the time. Show up.
#5. They Quit to Join a Hotter Startup When Growth Slowed
This last one stings because it often catches CEOs off-guard.
Here’s the scenario: Growth was 3x. Then it slowed to 2x. Then it’s looking like maybe 1.5x next year. Still growing! Still a good business! But not the rocketship it was.
And suddenly the CRO gets an offer from the hot new AI startup. And they take it.
I saw this happen at least three times this year.
I get it. CROs optimize for career trajectory just like everyone else. A slower-growth company is harder to sell as your next career chapter. The comp might be lower. The equity upside isn’t as exciting.
But here’s what these CROs missed: the companies that build enduring value aren’t always the fastest-growing. And the CROs who actually build their careers — who become true operating executives — are the ones who stick around when things get hard.
Growing 3x is one skill. Getting a company from $30M to $100M when growth has decelerated? That’s a completely different skill. And it’s a much rarer one.
The CROs who bailed when growth slowed? They never developed that second skill. They’re just chasing growth curves, and eventually, that catches up with you.
If you’re a CEO, watch for this. When growth slows, have the direct conversation with your CRO about commitment. And if you’re a CRO, understand that your reputation is built on what you accomplish when things are hard — not when everything’s working.
What’s NOT on This List?
You might notice something missing: “The CEO fired them because they missed the plan by a bit.”
I hear this one all the time. “CROs are on such a short leash. Miss one quarter and you’re out.”
In my experience? That’s more myth than reality.
Yes, CROs get fired. Yes, missing plan is often the proximate cause. But in almost every case I saw this year, the miss wasn’t really the issue. The issue was one of the five things above.
The CEO lost confidence because the CRO couldn’t actually sell the product. The board got worried because the CRO didn’t understand the partner channel. The team started churning because the CRO was never around.
The miss was just the moment when everyone admitted what they already knew.
Good CEOs don’t fire CROs for a tough quarter. They fire CROs when they lose confidence that the CRO can actually fix the problem. And that loss of confidence almost always traces back to one of these five root causes.
The Bottom Line
If you’re a CRO reading this, ask yourself honestly:
- When’s the last time you personally closed a deal?
- Could you give a deep-dive product demo to a technical buyer right now?
- Do you really understand your partner channel?
- When’s the last time you visited each of your major teams in person?
- If growth slows 30%, are you staying or going?
If you don’t like your answers, you’ve got work to do.
And if you’re a CEO who’s thinking about hiring a CRO, these are your interview questions. Not “tell me about a time you scaled a team” — but “how many deals did you personally close in your first 90 days at your last company?”
The CROs who succeed aren’t just managers with playbooks. They’re closers who learn, leaders who show up, and executives who stay when it gets hard.
That’s the job. The rest is just noise.
